Triethylamine → 6,6-Dimethylbicyclo[3.1.1]heptane

HRID 1723536Notes

Reaction equation

HRID 1723536 reaction equation
O[C@H:2]1[CH2:7][C@H:6]2[CH2:8][C@H:4]([C:5]2([CH3:10])[CH3:9])[C@@H:3]1CCOC1CCCO1.C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl.CCOCC>[CH3:9][C:5]1([CH3:10])[CH:6]2[CH2:8][CH:4]1[CH2:3][CH2:2][CH2:7]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57241612HCID 57241612, compound

Product 1

HCID 123134396,6-Dimethylbicyclo[3.1.1]heptaneYield 252%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 13 g of (1S,2S,3S,5R)-3-hydroxy-6,6-dimethyl-2-[2-(tetrahydrofuran-2-yloxy)-ethyl]bicyclo[3.1.1]heptane 14 [Jap. Unexamined Pat. Pub. No. 13551/1983] in 130 ml of dichloromethane is added 9.9 ml of triethylamine in a stream of nitrogen and then 6.16 g of methanesulfonyl chloride is dropwise added at -20° C., and the resulting mixture is stirred at the same temperature for 15 minutes. The reaction mixture is diluted with ether, washed with water, a saturated aqueous solution of ammonium chloride and a saturated sodium chloride aqueous solution successively, dried over sodium sulfate, and evaporated under reduced pressure to give 16 g of the titled compound 14a, of which the physical constant is as follows.

Workup

  1. washwashed with water
  2. dry with materiala saturated aqueous solution of ammonium chloride and a saturated sodium chloride aqueous solution successively, dried over sodium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-83560b09d53649748659502b2475a787
Source dataset
uspto-grants-1989_08
Patent number
US04861913

Reaction notes

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